JPS5782398A - 2-deoxystreptamine aminoglycoside derivative - Google Patents

2-deoxystreptamine aminoglycoside derivative

Info

Publication number
JPS5782398A
JPS5782398A JP56148680A JP14868081A JPS5782398A JP S5782398 A JPS5782398 A JP S5782398A JP 56148680 A JP56148680 A JP 56148680A JP 14868081 A JP14868081 A JP 14868081A JP S5782398 A JPS5782398 A JP S5782398A
Authority
JP
Japan
Prior art keywords
aprosaminide
beta
alpha
gentamine
protected
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP56148680A
Other languages
Japanese (ja)
Inventor
Andoriyuu Kaasuto Haabaato
Areshia Teyuruuderu Burenda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of JPS5782398A publication Critical patent/JPS5782398A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
    • C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
    • C07H15/224—Cyclohexane rings substituted by at least two nitrogen atoms with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/22—Cyclohexane rings, substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Novel 1-N-acylated or 1-N-alkylated derivatives of a 4-O-substituted-2-deoxystreptamine aminoglycoside selected from the group consisting of; apramycin, alpha or beta -(C1 to C6 alkyl)aprosaminide, alpha or beta -(C2 to C6 hydroxyalkyl)aprosaminide, alpha or beta -(C2 to C6 aminoalkyl)aprosaminide, alpha or beta -(C2 to C6 protected aminoalkyl) aprosaminide, alpha or beta -(C3 to C6 aminohydroxyalkyl)-aprosaminide, alpha or beta -(C3 to C6 (protected amino)hydroxyalkyl)aprosaminide, and pharmaceutically-acceptable acid addition salts thereof are disclosed. They are useful for treating warm blooded animals suffering from bacterial diseases. They and 1-N-acylated and 1-N-alkylated derivatives of lividamine, paromamine and the 6 min -N-protected derivatives of nebramine, neamine, gentamine C1, gentamine C1a, gentamine C2, gentamine C2a, and gentamine C2b, and pharmaceutically-acceptable acid addition salts thereof can be prepared by reacting the corresponding aminoglycoside substrate with a zinc salt Zn (X2), X being C1 to C10 carboxylate, in water, diluting with a polar organic solvent, treating with an alkalating agent or acylating agent, optionally, deprotecting the amino or N-protected substituents, optionally, reducing carbonyl portions of an acyl group, and recovering as a free base or as a pharmaceutically-acceptable acid addition salt.
JP56148680A 1980-09-22 1981-09-19 2-deoxystreptamine aminoglycoside derivative Pending JPS5782398A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18923180A 1980-09-22 1980-09-22

Publications (1)

Publication Number Publication Date
JPS5782398A true JPS5782398A (en) 1982-05-22

Family

ID=22696498

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56148680A Pending JPS5782398A (en) 1980-09-22 1981-09-19 2-deoxystreptamine aminoglycoside derivative

Country Status (5)

Country Link
EP (1) EP0048614B1 (en)
JP (1) JPS5782398A (en)
AT (1) ATE12235T1 (en)
DE (1) DE3169407D1 (en)
GB (1) GB2084148B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017018528A1 (en) * 2015-07-30 2017-02-02 公益財団法人 微生物化学研究会 Novel aminoglycoside antibiotic effective against multidrug-resistant bacteria

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4468513A (en) * 1980-09-22 1984-08-28 Eli Lilly And Company 2'-N-Acylated and 2'-N-alkylated derivatives of 4-O-substituted-2-deoxystreptamine aminoglycosides
GB2584009B (en) 2017-08-28 2022-03-23 Revagenix Inc Aminoglycosides and uses thereof
WO2019194858A1 (en) 2018-04-03 2019-10-10 Achaogen, Inc. Modular synthesis of aminoglycosides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017018528A1 (en) * 2015-07-30 2017-02-02 公益財団法人 微生物化学研究会 Novel aminoglycoside antibiotic effective against multidrug-resistant bacteria
US10617704B2 (en) 2015-07-30 2020-04-14 Microbial Chemistry Research Foundation Effective aminoglycoside antibiotic for multidrug-resistant bacteria
US11135234B2 (en) 2015-07-30 2021-10-05 Microbial Chemistry Research Foundation Effective aminoglycoside antibiotic for multidrug-resistant bacteria

Also Published As

Publication number Publication date
DE3169407D1 (en) 1985-04-25
GB2084148A (en) 1982-04-07
GB2084148B (en) 1984-08-15
ATE12235T1 (en) 1985-04-15
EP0048614A1 (en) 1982-03-31
EP0048614B1 (en) 1985-03-20

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